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Boc-D-Ala(adamantyl)-OH
Nom chimique: N-alpha-(t-Butyloxycarbonylamino)-1-adamantyl-D-alanine // Synonymes: Boc-Ala(Adamantyl)-OH, (R)-Boc-1-adamantyl-alanine, (2R)-3-((1s,3S)-adamantan-1-yl)-2-((tert-butoxycarbonyl)amino)propanoic acid
- n° Art.:BAA4800
- n° CAS:80972-86-7
- Formule:C18H29NO4
- Storage temperature:2-8°C
- Masse moléculaire:323,43 g/mol
from 3 000,00 €
description
The highly lipophilic, bulky adamantyl motif is a promising and validated building block to increase the drug-qualities of lead compounds without increasing their toxicity. See also BAA4590 Boc-L-Ala(adamantyl)-OH.
references
Tumor-Cell-Targeted Methionine-enkephalin Analogues Containing Unnatural Amino Acids: Design, Synthesis, and in Vitro Antitumor Activity; S. Horvat, K. Mlinariæ-Majerski, L. Glavaš-Obrovac, A. Jakas, J. Veljkoviæ, S. Marczi, G. Kragol, M. Rošèiæ, M. Matkoviæ, A. Milostiæ-Srb; J. Med. Chem. 2006; 49(11): 3136-3142. https://doi.org/10.1021/jm051026+
An Adamantyl Amino Acid Containing Gramicidin S Analogue with Broad Spectrum Antibacterial Activity and Reduced Hemolytic Activity; V. V. Kapoerchan, A. D. Knijnenburg, M. Niamat, E. Spalburg, A. J. de Neeling, P. H. Nibbering, R. H. Mars-Groenendijk, D. Noort, J. M. Otero, A. L. Llamas-Saiz, M. J. van Raaij, G. A. van der Marel, H. S. Overkleeft, M. Overhand; Chem.
Eur. J. 2010; 16(40): 12174-12181. https://doi.org/10.1002/chem.201001686
Tuning hydrophobicity of highly cationic tetradecameric Gramicidin S analogues using adamantane amino acids; A. D. Knijnenburg, V. V. Kapoerchan, E. Spalburg, A. J. de Neeling, R. H. Mars-Groenendijk, D. Noort, G. A. van der Marel, H. S. Overkleeft, M. Overhand; Bioorg. Med. Chem. 2010; 18(23): 8403-8409. https://doi.org/10.1016/j.bmc.2010.09.018
‘Inverted’ analogs of the antibiotic gramicidin S with an improved biological profile; V. V. Kapoerchan, A. D. Knijnenburg, P. Keizer, E. Spalburg, A. J. de Neeling, R. H. Mars-Groenendijk, D. Noort, J. M. Otero, A. L. Llamas-Saiz, M. J. van Raaij, G. A. van der Marel, H. S. Overkleeft, M. Overhand; Bioorg. Med. Chem. 2012; 20(20): 6059-6062. https://doi.org/10.1016/j.bmc.2012.08.038
Structure-activity relationship study of the tumour-targeting peptide A20FMDV2 via modification of Lys16, Leu13, and N- and/or C-terminal functionality; K.-Y. Hung, P. W. R. Harris, A. Desai, J. F. Marshall, M. A. Brimble; Eur. J. Med. Chem. 2017; 136: 154-164 . https://doi.org/10.1016/j.ejmech.2017.05.008
Structure-Based Design of Non-natural Macrocyclic Peptides That Inhibit Protein-Protein Interactions; D. M. Krüger, A. Glas, D. Bier, N. Pospiech, K. Wallraven, L. Dietrich, C. Ottmann, O. Koch, S. Hennig, T. N. Grossmann; J. Med. Chem. 2017; 60(21): 8982-8988. https://doi.org/10.1021/acs.jmedchem.7b01221
J. Müller, R. A. Kirschner, J.-P. Berndt, T. Wulsdorf, A. Metz, R. Hrdina, P. R. Schreiner, A. Geyer, G. Klebe; ChemMedChem 2019; 14: 663-672. https://doi.org/10.1002/cmdc.201800779
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All information contained in our webshop is compiled to the best of our knowledge.
Prices and product availability are subject to change and require reconfirmation. Please contact us for further information.
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